@T_Schneider , For the error message we get, it shows access is denied. Please go to "C:\windows\system32\windowspowershell\v1.0" and find Powershell.exe. Check the permission for the account that runs the Operation Manager agent like local system and see if it has read & execute rights. If not, grant the permission to see if it is working.
However, if the issue still persists, please clear cache to see if it can be fixed.
https://learn.microsoft.com/en-us/system-center/scom/manage-clear-healthservice-cache?view=sc-om-2019
In addition, I notice you doubt it may be related with windows updates. To clarify this, we can uninstall the patch one by one to see if we can find the one that may be related.
Hope it can help.
If the response is helpful, please click "Accept Answer" and upvote it.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.